ol0068997_si_001.pdf (1.13 MB)
Synthesis of the Left-Hand Portion of Geldanamycin Using an Anti Glycolate Aldol Reaction
journal contribution
posted on 2000-12-23, 00:00 authored by Merritt B. Andrus, Erik L. Meredith, B. B. V. Soma SekharA synthesis of the left-hand portion of the ansamycin antitumor natural product geldanamycin is reported. An advanced intermediate incorporates
the methoxyquinone precursor as a pentasubstituted benzene with a 10-carbon chain that contains 4 of the 6 stereocenters. The key reaction
is a novel anti glycolate aldol reaction with a new diaryl-4-oxapyrone used to generate the C-11, C-12 hydroxy, methoxy functionality.